1,4,10,19,25,41,55,60,67,69-Decakis(trifluoro­meth­yl)-1,4,10,19,25,41,55,60,67,69-deca­hydro­(C70-D5h)[5,6]fullerene

Shustova, N.B.; Peryshkov, D.V.; Boltalina, O.V.; Strauss, S.H.

doi:10.1107/S1600536807043991

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1,4,10,19,25,41,55,60,67,69-Decakis(trifluoromethyl)-1,4,10,19,25,41,55,60,67,69-decahydro(C₇₀-D_5h)[5,6]fullerene

N. B. Shustova, D. V. Peryshkov, O. V. Boltalina and S. H. Strauss

The title compound, C₈₀F₃₀, is one of seven isomers of C₇₀(CF₃)₁₀ that have been isolated. The C₂-symmetry fullerene molecule has an idealized D_5h C₇₀ core with the ten CF₃ groups arranged on a `pole-to-pole' para-meta-para-para-para-para-para-meta-para (pmp⁵mp) ribbon of edge-sharing C₆(CF₃)₂ hexagons. There are no cage Csp³—Csp³ bonds. There are intramolecular F

F contacts between pairs of CF₃ groups on the same hexagon that range from 2.560 (3) to 2.876 (3) Å. Two CF₃ groups are disordered with almost equal occupancies.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043991/om2161sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043991/om2161Isup2.hkl Contains datablock I

CCDC reference: 663777

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.053
wR factor = 0.124
Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT213_ALERT_2_B Atom F11     has ADP max/min Ratio .............       4.40 prola
PLAT220_ALERT_2_B Large Non-Solvent    F     Ueq(max)/Ueq(min) ...       3.62 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT040_ALERT_1_C No H-atoms in this Carbon Containing Compound ..          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT213_ALERT_2_C Atom F12     has ADP max/min Ratio .............       3.90 prola
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C74
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C75
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  F6     ..  C22     ..       2.92 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  F8     ..  C16     ..       2.96 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      37.00 A   3 
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.40 Deg.
              C75  -C19  -C75A    1.555   1.555   1.555

Alert level G
CHEMS02_ALERT_1_G  Please check that you have entered the correct
            _publ_requested_category classification of your compound;
            FI or CI or EI for inorganic; FM or CM or EM for metal-organic;
            FO or CO or EO for organic.
            From the CIF: _publ_requested_category   EO
            From the CIF: _chemical_formula_sum:C80 F30
PLAT793_ALERT_1_G Check the Absolute Configuration of C10    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C25    = ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         25

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Recently reported high-temperature reactions of C₇₀ with CF₃I have yielded more than two dozen C₇₀(CF₃)_n derivatives (n = 2–18), most with relatively stable addition patterns that are chiral as well as unprecedented in fullerene(X)_n chemistry (Kareev, Kuvychko, Lebedkin et al., 2005; Kareev et al., 2006a; Kareev et al., 2006b; Avdoshenko et al., 2006; Goryunkov et al., 2006; Ignat'eva et al., 2006; Popov, Kareev, Shustova et al., 2007; Shustova, Peryshkov, Kareev, et al., 2007). A member of the n = 10 set of seven isomers (Popov, Kareev, Shustova et al., 2007), the title compound has been crystallized from toluene and we report its crystal structure here.

The structure of the title compound, as shown in Figs. 1 and 2, comprises an idealized D_{5 h} C₇₀ core with ten sp³ carbon atoms at positions 1, 4, 10, 19, 25, 41, 55, 60, 67, and 69 (Powell et al., 2002), each of which is attached to a CF₃ group. The cage sp³ carbon atoms are not adjacent to one another. The CF₃ groups are arranged on a para-meta-para-para-para-para-para- meta-para (pmp⁵mp) ribbon of edge-sharing C₆(CF₃)₂ hexagons. The shared edges in each ribbon of hexagons are C(sp³)-C(sp²) bonds (e.g., C1—C2, C4—C5, etc.), not C(sp²)-C(sp²) bonds. Thus, any pair of adjacent hexagons along the ribbon has a common CF₃ group.

The two CF₃ groups in the middle of the ribbon are disordered and were refined as half atoms. Only one set of the two disordered pairs is shown in the figures. As in all other published structures of fullerene(CF₃)_n compounds, there are F^···F intramolecular contacts between pairs of neighboring CF₃ groups. The range of F^···F distances that do not involve the disordered CF₃ groups is from 2.539 (3) to 2.756 (3) Å. The range of C^···F distances that do not involve the disordered CF₃ groups is from 1.323 (3) to 1.338 (3) Å.

The shortest cage C—C bond in the asymmetric unit is C8—C9, at 1.349 (4) Å. This is significantly shorter than the shortest C—C bond of this type in the most precise structure of empty C₇₀ reported to date (C₉H₃Cl₆N^.3(C₇₀)^.3(C₆H₅Cl)), which is 1.440 (4) Å (Pham et al., 2007). More importantly, the C8—C9 bond is a pentagon-hexagon junction, and the shortest pent-hex junction in C₉H₃Cl₆N^.3(C₇₀)^.3(C₆H₅Cl)) is also 1.440 (4) Å (the longest pent-hex junction in C₉H₃Cl₆N^.3(C₇₀)^.3(C₆H₅Cl)) is 1.460 (4) Å.

Related literature top

For related literature, see: Avdoshenko et al. (2006); Goryunkov et al. (2006); Ignat'eva et al. (2006); Kareev et al. (2005, 2006a,b); Pham et al. (2007); Popov et al. (2007); Powell et al. (2002); Shustova et al. (2007).

Experimental top

The synthesis of the title compound was carried out by heating C₇₀ in a stream of CF₃I at 420 °C as previously described (Popov, Kareev, Shustova, et al. 2007). Crystals of the HPLC-purified compound were grown by slow evaporation of a saturated deuterochloroform solution.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: APEX2 (Bruker, 2000); data reduction: APEX2 (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level. The crystallographic C₂ axis is perpendicular to the plane of the page. Only one pair of the disordered CF₃ groups on the hexagon centered on the C₂ axis is shown.

Fig. 2. (Left) Schlegel diagram showing the IUPAC lowest-locants for the cage carbon atoms. The C₂ axis passes through the center of the hexagon with C19 and C41 and bisects the C30—C50 bond. The CF₃ groups are attached to the cage carbon atoms depicted as black circles. Also shown is the ribbon of meta- and para-C₆(CF₃)₂ edge-sharing hexagons (the two meta-C₆(CF₃)₂ hexagons are indicated with the letter m). (Right) The structure showing the atom numbers for the CF₃ groups and the network of F^···F contacts between CF₃ groups that share the same hexagon.

1,4,10,19,25,41,55,60,67,69-Decakis(trifluoromethyl)- 1,4,10,19,25,41,55,60,67,69-decahydro(C₇₀—D_{5 h})[5,6]fullerene top

Crystal data top

C₈₀F₃₀	D_x = 2.012 Mg m⁻³
M_r = 1530.80	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 999 reflections
a = 16.0658 (3) Å	θ = 1.7–27.9°
b = 17.2662 (4) Å	µ = 0.20 mm⁻¹
c = 18.2153 (4) Å	T = 100 K
V = 5052.84 (19) Å³	Plate, red
Z = 4	0.44 × 0.10 × 0.05 mm
F(000) = 3000

Data collection top

Bruker Kappa APEXII diffractometer	5853 independent reflections
Radiation source: fine-focus sealed tube	3409 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
φ and ω scans	θ_max = 27.9°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −19→21
T_min = 0.920, T_max = 0.990	k = −20→21
53138 measured reflections	l = −23→19

Refinement top

Refinement on F²	25 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.053	Secondary atom site location: difference Fourier map
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0456P)² + 4.0833P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.026
5853 reflections	Δρ_max = 0.47 e Å⁻³
534 parameters	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₈₀F₃₀	V = 5052.84 (19) Å³
M_r = 1530.80	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 16.0658 (3) Å	µ = 0.20 mm⁻¹
b = 17.2662 (4) Å	T = 100 K
c = 18.2153 (4) Å	0.44 × 0.10 × 0.05 mm

Data collection top

Bruker Kappa APEXII diffractometer	5853 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3409 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.990	R_int = 0.098
53138 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	534 parameters
wR(F²) = 0.124	25 restraints
S = 1.02	Δρ_max = 0.47 e Å⁻³
5853 reflections	Δρ_min = −0.54 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.14807 (15)	0.84689 (16)	0.57610 (14)	0.0172 (6)
C2	0.06726 (15)	0.89202 (16)	0.56364 (14)	0.0171 (6)
C3	−0.00314 (15)	0.85035 (16)	0.54804 (14)	0.0179 (6)
C4	−0.01274 (16)	0.76084 (17)	0.55711 (15)	0.0212 (7)
C5	0.05113 (16)	0.73164 (16)	0.61305 (15)	0.0192 (6)
C6	0.12706 (15)	0.76964 (16)	0.61409 (15)	0.0171 (6)
C7	0.18225 (15)	0.76010 (16)	0.67239 (15)	0.0181 (6)
C8	0.22979 (14)	0.83155 (16)	0.68340 (14)	0.0161 (6)
C9	0.20545 (14)	0.88497 (16)	0.63383 (14)	0.0158 (6)
C10	0.20897 (15)	0.97126 (16)	0.64795 (14)	0.0163 (6)
C11	0.12152 (15)	1.00488 (16)	0.63621 (15)	0.0169 (6)
C12	0.06016 (15)	0.97158 (16)	0.59058 (14)	0.0161 (6)
C13	−0.02077 (15)	1.00408 (16)	0.59698 (15)	0.0181 (6)
C14	−0.09317 (15)	0.96120 (17)	0.57594 (14)	0.0187 (6)
C15	−0.08409 (15)	0.88541 (18)	0.55430 (14)	0.0208 (7)
C16	−0.14344 (15)	0.82795 (17)	0.57804 (15)	0.0203 (7)
C17	−0.10068 (15)	0.75657 (17)	0.58928 (15)	0.0216 (7)
C18	−0.12203 (16)	0.71052 (17)	0.64672 (16)	0.0224 (7)
C19	−0.06088 (16)	0.65728 (16)	0.68667 (16)	0.0227 (7)
C20	0.02896 (16)	0.68342 (16)	0.67393 (16)	0.0213 (7)
C21	0.08471 (16)	0.67492 (16)	0.73207 (16)	0.0219 (7)
C22	0.16204 (15)	0.71231 (16)	0.73075 (15)	0.0201 (6)
C23	0.18732 (15)	0.73373 (17)	0.80518 (15)	0.0208 (7)
C24	0.23331 (15)	0.79965 (17)	0.81776 (15)	0.0191 (6)
C25	0.27335 (15)	0.84797 (16)	0.75587 (15)	0.0196 (6)
C26	0.24996 (15)	0.93044 (17)	0.77931 (15)	0.0188 (6)
C27	0.21993 (15)	0.98455 (16)	0.73100 (14)	0.0179 (6)
C28	0.15831 (16)	1.03892 (16)	0.75525 (15)	0.0193 (6)
C29	0.09863 (16)	1.05095 (16)	0.69643 (15)	0.0187 (6)
C30	0.01394 (16)	1.07106 (15)	0.71141 (15)	0.0174 (6)
C31	−0.04340 (15)	1.05362 (16)	0.65680 (15)	0.0173 (6)
C32	−0.13118 (15)	1.04049 (16)	0.67284 (15)	0.0185 (6)
C33	−0.16206 (15)	0.98408 (17)	0.62258 (15)	0.0203 (6)
C45	0.20949 (15)	0.84927 (17)	0.87587 (15)	0.0209 (7)
C46	0.21946 (15)	0.92902 (17)	0.85350 (15)	0.0203 (7)
C71	0.36707 (16)	0.83212 (18)	0.75032 (16)	0.0232 (7)
C72	0.27308 (16)	1.01737 (17)	0.60260 (15)	0.0208 (6)
C73	0.19695 (16)	0.83397 (17)	0.50429 (15)	0.0218 (7)
C74	−0.00903 (18)	0.7147 (2)	0.48471 (18)	0.0334 (8)
F1	0.40336 (9)	0.87577 (10)	0.69942 (9)	0.0298 (4)
F2	0.40463 (9)	0.84669 (11)	0.81408 (9)	0.0356 (5)
F3	0.38117 (10)	0.75794 (10)	0.73328 (10)	0.0354 (5)
F4	0.34564 (9)	0.98094 (10)	0.59759 (9)	0.0324 (4)
F5	0.24686 (9)	1.03264 (10)	0.53477 (8)	0.0281 (4)
F6	0.28737 (11)	1.08613 (10)	0.63398 (9)	0.0373 (5)
F7	0.24219 (11)	0.89500 (11)	0.48588 (10)	0.0401 (5)
F8	0.24879 (11)	0.77447 (11)	0.51097 (9)	0.0424 (5)
F9	0.14794 (10)	0.81972 (11)	0.44729 (9)	0.0376 (5)
F10	0.06645 (10)	0.69174 (11)	0.46686 (9)	0.0389 (5)
F11	−0.05481 (16)	0.65144 (16)	0.48843 (15)	0.1015 (12)
F12	−0.03764 (16)	0.75595 (16)	0.42896 (11)	0.0793 (9)
F13	−0.0496 (3)	0.5632 (3)	0.5902 (3)	0.053 (2)	0.511 (8)
F14	−0.0479 (5)	0.5247 (3)	0.7019 (4)	0.060 (3)	0.511 (8)
F15	−0.1603 (3)	0.5624 (4)	0.6519 (4)	0.0402 (15)	0.511 (8)
C75	−0.0798 (8)	0.5751 (6)	0.6567 (7)	0.021 (3)	0.511 (8)
F13A	−0.1288 (5)	0.5590 (4)	0.6213 (4)	0.0464 (19)	0.489 (8)
F14A	−0.0029 (3)	0.5355 (2)	0.6456 (4)	0.052 (2)	0.489 (8)
F15A	−0.0943 (4)	0.5270 (3)	0.7297 (3)	0.0397 (14)	0.489 (8)
C75A	−0.0701 (9)	0.5695 (6)	0.6721 (7)	0.026 (4)	0.489 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0157 (12)	0.0214 (16)	0.0144 (15)	−0.0016 (11)	0.0022 (11)	−0.0013 (13)
C2	0.0184 (13)	0.0260 (17)	0.0068 (13)	0.0017 (11)	0.0034 (10)	0.0004 (13)
C3	0.0195 (13)	0.0248 (17)	0.0094 (14)	−0.0003 (11)	0.0003 (11)	−0.0056 (13)
C4	0.0186 (14)	0.0266 (18)	0.0184 (16)	−0.0040 (12)	0.0028 (11)	−0.0114 (13)
C5	0.0203 (13)	0.0177 (16)	0.0196 (15)	0.0012 (11)	0.0043 (11)	−0.0097 (13)
C6	0.0166 (13)	0.0166 (16)	0.0182 (15)	0.0006 (11)	0.0056 (11)	−0.0055 (13)
C7	0.0127 (12)	0.0184 (16)	0.0231 (16)	0.0043 (11)	0.0049 (11)	−0.0021 (13)
C8	0.0114 (12)	0.0199 (16)	0.0170 (15)	0.0009 (10)	0.0036 (10)	−0.0018 (13)
C9	0.0137 (12)	0.0206 (16)	0.0130 (14)	−0.0009 (11)	0.0056 (10)	−0.0028 (13)
C10	0.0164 (12)	0.0186 (16)	0.0139 (14)	−0.0031 (11)	0.0000 (11)	−0.0009 (12)
C11	0.0210 (13)	0.0145 (15)	0.0153 (15)	−0.0021 (11)	0.0045 (11)	0.0035 (12)
C12	0.0204 (13)	0.0206 (17)	0.0073 (14)	0.0002 (11)	0.0020 (11)	0.0038 (12)
C13	0.0224 (14)	0.0208 (17)	0.0109 (15)	0.0017 (11)	0.0016 (11)	0.0052 (13)
C14	0.0187 (13)	0.0283 (18)	0.0092 (14)	0.0046 (12)	−0.0030 (10)	0.0050 (13)
C15	0.0176 (13)	0.037 (2)	0.0075 (14)	0.0006 (12)	−0.0022 (11)	−0.0045 (13)
C16	0.0169 (13)	0.0309 (18)	0.0133 (15)	−0.0002 (12)	−0.0059 (11)	−0.0079 (13)
C17	0.0154 (13)	0.0305 (18)	0.0188 (16)	−0.0068 (12)	0.0001 (11)	−0.0135 (14)
C18	0.0193 (13)	0.0237 (17)	0.0242 (17)	−0.0070 (12)	0.0012 (12)	−0.0120 (14)
C19	0.0218 (14)	0.0168 (17)	0.0294 (17)	−0.0046 (11)	0.0076 (12)	−0.0073 (14)
C20	0.0199 (13)	0.0136 (16)	0.0305 (18)	−0.0005 (11)	0.0073 (12)	−0.0088 (14)
C21	0.0215 (14)	0.0111 (15)	0.0332 (18)	0.0027 (11)	0.0083 (12)	0.0012 (13)
C22	0.0161 (13)	0.0172 (16)	0.0272 (17)	0.0059 (11)	0.0044 (12)	0.0020 (14)
C23	0.0159 (13)	0.0227 (17)	0.0237 (16)	0.0071 (11)	0.0014 (12)	0.0080 (14)
C24	0.0115 (12)	0.0268 (18)	0.0190 (15)	0.0054 (11)	−0.0003 (11)	0.0086 (13)
C25	0.0138 (12)	0.0265 (17)	0.0185 (15)	0.0000 (11)	−0.0001 (11)	0.0031 (14)
C26	0.0107 (12)	0.0283 (17)	0.0174 (15)	−0.0040 (11)	0.0003 (11)	−0.0010 (14)
C27	0.0162 (12)	0.0206 (16)	0.0168 (15)	−0.0077 (11)	0.0008 (11)	−0.0025 (13)
C28	0.0199 (13)	0.0170 (16)	0.0209 (16)	−0.0075 (11)	0.0027 (11)	−0.0023 (13)
C29	0.0238 (14)	0.0133 (16)	0.0191 (16)	−0.0032 (11)	0.0032 (12)	0.0064 (13)
C30	0.0263 (14)	0.0072 (14)	0.0187 (15)	0.0004 (11)	0.0029 (12)	0.0011 (12)
C31	0.0214 (13)	0.0157 (16)	0.0150 (15)	0.0039 (11)	0.0027 (11)	0.0070 (12)
C32	0.0205 (13)	0.0201 (16)	0.0147 (15)	0.0085 (11)	−0.0006 (11)	0.0050 (13)
C33	0.0180 (13)	0.0288 (18)	0.0140 (15)	0.0082 (12)	−0.0034 (11)	0.0061 (13)
C45	0.0126 (12)	0.0342 (19)	0.0161 (15)	0.0017 (12)	−0.0060 (11)	0.0053 (14)
C46	0.0123 (12)	0.0337 (19)	0.0148 (15)	−0.0040 (12)	−0.0046 (11)	0.0005 (14)
C71	0.0151 (13)	0.033 (2)	0.0218 (16)	0.0016 (12)	−0.0007 (12)	0.0051 (15)
C72	0.0211 (14)	0.0236 (18)	0.0177 (16)	−0.0044 (12)	−0.0005 (11)	−0.0014 (14)
C73	0.0168 (13)	0.0291 (18)	0.0194 (16)	−0.0016 (12)	0.0018 (12)	−0.0023 (14)
C74	0.0258 (16)	0.043 (2)	0.0315 (19)	−0.0086 (15)	0.0094 (14)	−0.0174 (17)
F1	0.0171 (8)	0.0452 (12)	0.0270 (10)	−0.0027 (7)	0.0034 (7)	0.0059 (9)
F2	0.0168 (8)	0.0643 (13)	0.0256 (10)	−0.0002 (8)	−0.0042 (7)	0.0052 (9)
F3	0.0215 (8)	0.0346 (12)	0.0501 (12)	0.0089 (7)	0.0046 (8)	0.0034 (9)
F4	0.0177 (8)	0.0434 (11)	0.0361 (11)	−0.0030 (7)	0.0064 (7)	0.0092 (9)
F5	0.0277 (8)	0.0388 (11)	0.0177 (9)	−0.0057 (7)	0.0022 (7)	0.0079 (8)
F6	0.0518 (11)	0.0297 (11)	0.0302 (10)	−0.0222 (8)	0.0131 (8)	−0.0067 (9)
F7	0.0467 (11)	0.0412 (12)	0.0325 (11)	−0.0192 (9)	0.0217 (9)	−0.0082 (9)
F8	0.0464 (11)	0.0493 (13)	0.0315 (11)	0.0266 (9)	0.0178 (9)	0.0039 (10)
F9	0.0282 (9)	0.0677 (14)	0.0168 (9)	−0.0052 (9)	0.0048 (7)	−0.0127 (9)
F10	0.0309 (10)	0.0548 (13)	0.0310 (11)	0.0059 (9)	0.0081 (8)	−0.0190 (9)
F11	0.0947 (18)	0.101 (2)	0.109 (2)	−0.0763 (16)	0.0727 (17)	−0.0905 (18)
F12	0.0927 (18)	0.112 (2)	0.0335 (13)	0.0535 (15)	−0.0346 (12)	−0.0437 (14)
F13	0.071 (4)	0.036 (3)	0.054 (3)	−0.021 (2)	0.030 (3)	−0.026 (2)
F14	0.088 (6)	0.021 (3)	0.072 (5)	−0.001 (3)	−0.054 (5)	0.001 (3)
F15	0.025 (2)	0.031 (3)	0.064 (4)	−0.008 (2)	−0.003 (2)	−0.016 (3)
C75	0.018 (5)	0.016 (6)	0.028 (6)	−0.002 (4)	−0.001 (4)	−0.005 (4)
F13A	0.066 (5)	0.024 (3)	0.049 (4)	−0.004 (3)	−0.029 (4)	−0.007 (3)
F14A	0.039 (3)	0.021 (3)	0.096 (6)	−0.0068 (18)	0.038 (3)	−0.022 (3)
F15A	0.064 (4)	0.020 (2)	0.036 (3)	−0.011 (2)	0.006 (2)	0.001 (2)
C75A	0.019 (5)	0.040 (9)	0.019 (6)	−0.004 (5)	0.002 (4)	−0.003 (5)

Geometric parameters (Å, º) top

C1—C2	1.531 (4)	C21—C19ⁱ	1.559 (4)
C1—C6	1.540 (4)	C22—C23	1.463 (4)
C1—C73	1.542 (4)	C23—C24	1.376 (4)
C1—C9	1.545 (4)	C23—C18ⁱ	1.424 (4)
C2—C3	1.370 (4)	C24—C45	1.415 (4)
C2—C12	1.463 (4)	C24—C25	1.543 (4)
C3—C15	1.439 (4)	C25—C26	1.533 (4)
C3—C4	1.562 (4)	C25—C71	1.534 (4)
C4—C17	1.531 (4)	C26—C27	1.371 (4)
C4—C5	1.531 (4)	C26—C46	1.438 (4)
C4—C74	1.542 (4)	C27—C28	1.434 (4)
C5—C6	1.385 (4)	C28—C32ⁱ	1.381 (4)
C5—C20	1.432 (4)	C28—C29	1.453 (4)
C6—C7	1.393 (4)	C29—C30	1.430 (4)
C7—C22	1.384 (4)	C30—C31	1.389 (4)
C7—C8	1.465 (4)	C30—C30ⁱ	1.475 (5)
C8—C9	1.349 (4)	C31—C32	1.458 (4)
C8—C25	1.521 (4)	C32—C28ⁱ	1.381 (4)
C9—C10	1.513 (4)	C32—C33	1.426 (4)
C10—C11	1.535 (3)	C33—C46ⁱ	1.394 (4)
C10—C27	1.540 (4)	C45—C16ⁱ	1.402 (4)
C10—C72	1.542 (4)	C45—C46	1.445 (4)
C11—C29	1.404 (4)	C46—C33ⁱ	1.394 (4)
C11—C12	1.412 (4)	C71—F1	1.330 (3)
C12—C13	1.421 (4)	C71—F2	1.333 (3)
C13—C14	1.431 (4)	C71—F3	1.337 (3)
C13—C31	1.432 (4)	C72—F4	1.328 (3)
C14—C15	1.374 (4)	C72—F5	1.332 (3)
C14—C33	1.450 (4)	C72—F6	1.338 (3)
C15—C16	1.442 (4)	C73—F7	1.323 (3)
C16—C45ⁱ	1.402 (4)	C73—F9	1.326 (3)
C16—C17	1.426 (4)	C73—F8	1.328 (3)
C17—C18	1.358 (4)	C74—F10	1.316 (3)
C18—C23ⁱ	1.424 (4)	C74—F11	1.319 (4)
C18—C19	1.530 (4)	C74—F12	1.323 (4)
C19—C20	1.530 (4)	F13—C75	1.322 (12)
C19—C75	1.551 (10)	F14—C75	1.303 (12)
C19—C75A	1.546 (11)	F15—C75	1.315 (12)
C19—C21ⁱ	1.559 (4)	F13A—C75A	1.332 (13)
C20—C21	1.395 (4)	F14A—C75A	1.321 (13)
C21—C22	1.400 (4)	F15A—C75A	1.339 (13)

C2—C1—C6	108.8 (2)	C7—C22—C23	119.7 (2)
C2—C1—C73	112.3 (2)	C21—C22—C23	110.3 (2)
C6—C1—C73	111.6 (2)	C24—C23—C18ⁱ	121.7 (3)
C2—C1—C9	113.0 (2)	C24—C23—C22	120.8 (3)
C6—C1—C9	101.2 (2)	C18ⁱ—C23—C22	107.1 (2)
C73—C1—C9	109.6 (2)	C23—C24—C45	118.7 (2)
C3—C2—C12	119.9 (2)	C23—C24—C25	123.3 (3)
C3—C2—C1	117.6 (2)	C45—C24—C25	109.4 (2)
C12—C2—C1	119.6 (2)	C8—C25—C26	107.6 (2)
C2—C3—C15	120.6 (3)	C8—C25—C71	111.2 (2)
C2—C3—C4	125.4 (2)	C26—C25—C71	115.1 (2)
C15—C3—C4	108.6 (2)	C8—C25—C24	110.0 (2)
C17—C4—C5	110.4 (2)	C26—C25—C24	101.3 (2)
C17—C4—C74	109.8 (2)	C71—C25—C24	111.2 (2)
C5—C4—C74	111.9 (2)	C27—C26—C46	119.7 (2)
C17—C4—C3	100.3 (2)	C27—C26—C25	122.7 (2)
C5—C4—C3	109.3 (2)	C46—C26—C25	109.2 (2)
C74—C4—C3	114.6 (2)	C26—C27—C28	119.4 (2)
C6—C5—C20	118.9 (2)	C26—C27—C10	124.7 (2)
C6—C5—C4	116.3 (2)	C28—C27—C10	108.7 (2)
C20—C5—C4	122.7 (2)	C32ⁱ—C28—C27	121.5 (3)
C5—C6—C7	121.0 (3)	C32ⁱ—C28—C29	119.2 (2)
C5—C6—C1	126.7 (2)	C27—C28—C29	108.8 (2)
C7—C6—C1	107.8 (2)	C11—C29—C30	122.4 (2)
C22—C7—C6	120.4 (2)	C11—C29—C28	108.8 (2)
C22—C7—C8	121.3 (2)	C30—C29—C28	121.5 (2)
C6—C7—C8	109.7 (2)	C31—C30—C29	116.2 (2)
C9—C8—C7	109.5 (2)	C31—C30—C30ⁱ	118.8 (3)
C9—C8—C25	126.0 (2)	C29—C30—C30ⁱ	118.1 (3)
C7—C8—C25	121.0 (2)	C30—C31—C13	120.4 (2)
C8—C9—C10	123.3 (2)	C30—C31—C32	122.1 (2)
C8—C9—C1	109.7 (2)	C13—C31—C32	107.8 (2)
C10—C9—C1	123.9 (2)	C28ⁱ—C32—C33	119.1 (3)
C9—C10—C11	108.3 (2)	C28ⁱ—C32—C31	119.9 (2)
C9—C10—C27	108.5 (2)	C33—C32—C31	108.3 (2)
C11—C10—C27	100.7 (2)	C46ⁱ—C33—C32	119.7 (2)
C9—C10—C72	116.3 (2)	C46ⁱ—C33—C14	120.1 (3)
C11—C10—C72	110.0 (2)	C32—C33—C14	107.3 (2)
C27—C10—C72	111.9 (2)	C16ⁱ—C45—C24	119.6 (3)
C29—C11—C12	120.5 (2)	C16ⁱ—C45—C46	120.2 (3)
C29—C11—C10	110.2 (2)	C24—C45—C46	109.6 (2)
C12—C11—C10	124.5 (2)	C33ⁱ—C46—C26	120.5 (3)
C11—C12—C13	115.5 (2)	C33ⁱ—C46—C45	119.2 (2)
C11—C12—C2	121.7 (2)	C26—C46—C45	108.6 (2)
C13—C12—C2	118.0 (2)	F1—C71—F2	107.6 (2)
C12—C13—C14	121.2 (2)	F1—C71—F3	107.9 (2)
C12—C13—C31	122.0 (2)	F2—C71—F3	107.8 (2)
C14—C13—C31	107.8 (2)	F1—C71—C25	112.0 (2)
C15—C14—C13	118.9 (2)	F2—C71—C25	110.7 (2)
C15—C14—C33	120.6 (3)	F3—C71—C25	110.6 (2)
C13—C14—C33	108.8 (2)	F4—C72—F5	107.9 (2)
C14—C15—C3	121.3 (2)	F4—C72—F6	107.4 (2)
C14—C15—C16	119.9 (2)	F5—C72—F6	106.0 (2)
C3—C15—C16	109.4 (3)	F4—C72—C10	112.3 (2)
C45ⁱ—C16—C17	120.4 (3)	F5—C72—C10	112.8 (2)
C45ⁱ—C16—C15	119.9 (3)	F6—C72—C10	110.1 (2)
C17—C16—C15	108.6 (2)	F7—C73—F9	106.0 (2)
C18—C17—C16	119.7 (2)	F7—C73—F8	107.2 (2)
C18—C17—C4	123.8 (3)	F9—C73—F8	107.5 (2)
C16—C17—C4	110.4 (2)	F7—C73—C1	112.3 (2)
C17—C18—C23ⁱ	119.7 (3)	F9—C73—C1	112.9 (2)
C17—C18—C19	123.8 (2)	F8—C73—C1	110.7 (2)
C23ⁱ—C18—C19	110.5 (2)	F10—C74—F11	106.1 (3)
C18—C19—C20	110.9 (2)	F10—C74—F12	107.0 (3)
C18—C19—C75	104.9 (5)	F11—C74—F12	107.0 (3)
C20—C19—C75	113.7 (5)	F10—C74—C4	113.7 (2)
C18—C19—C75A	116.5 (6)	F11—C74—C4	111.3 (3)
C20—C19—C75A	110.7 (5)	F12—C74—C4	111.4 (3)
C75—C19—C75A	12.4 (8)	F14—C75—F13	109.3 (10)
C18—C19—C21ⁱ	100.2 (2)	F14—C75—F15	108.6 (9)
C20—C19—C21ⁱ	108.6 (2)	F13—C75—F15	105.9 (10)
C75—C19—C21ⁱ	117.7 (5)	F14—C75—C19	108.2 (8)
C75A—C19—C21ⁱ	109.4 (5)	F13—C75—C19	113.1 (8)
C21—C20—C5	119.3 (2)	F15—C75—C19	111.6 (8)
C21—C20—C19	117.4 (3)	F13A—C75A—F14A	105.4 (10)
C5—C20—C19	121.6 (2)	F13A—C75A—F15A	105.3 (9)
C20—C21—C22	120.5 (3)	F14A—C75A—F15A	106.2 (10)
C20—C21—C19ⁱ	125.7 (2)	F13A—C75A—C19	108.7 (9)
C22—C21—C19ⁱ	108.9 (2)	F14A—C75A—C19	114.8 (9)
C7—C22—C21	119.7 (3)	F15A—C75A—C19	115.5 (9)

Symmetry code: (i) −x, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₈₀F₃₀
M_r	1530.80
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	16.0658 (3), 17.2662 (4), 18.2153 (4)
V (Å³)	5052.84 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.44 × 0.10 × 0.05

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.920, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	53138, 5853, 3409
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.124, 1.02
No. of reflections	5853
No. of parameters	534
No. of restraints	25
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.54

Computer programs: APEX2 (Bruker, 2000), SHELXTL (Bruker, 2000).

Correspondence of IUPAC lowest locants with crystallographic atom numbers for C₂-1,4,10,19,25,41,55,60,67,69-C₇₀(CF₃)₁₀ top



C1	C1
C2	C2
C3	C3
C4	C4
C5	C5
C6	C6
C7	C7
C8	C8
C9	C9
C10	C10
C11	C11
C12	C12
C13	C13
C14	C14
C15	C15
C16	C16
C17	C17
C18	C18
C19	C19
C20	C20
C21	C21
C22	C22
C23	C23
C24	C24
C25	C25
C26	C26
C27	C27
C28	C28
C29	C29
C30	C30
C31	C31
C32	C32
C33	C33
C34	C46a
C35	C45a
C36	C24a
C37	C23a
C38	C22a
C39	C21a
C40	C20a
C41	C19a
C42	C18a
C43	C17a
C44	C16a
C45	C45
C46	C46
C47	C33a
C48	C32a
C49	C31a
C50	C30a
C51	C29a
C52	C28a
C53	C27a
C54	C26a
C55	C25a
C56	C8a
C57	C7a
C58	C6a
C59	C5a
C60	C4a
C61	C3a
C62	C15a
C63	C14a
C64	C13a
C65	C12a
C66	C11a
C67	C10a
C68	C9a
C69	C1a
C70	C2a

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